2-[13-[2-(4-Methoxyphenyl)ethynyl]pentacen-6-yl]ethynyl-tri(propan-2-yl)silane | 1051394-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 并五苯
• 英文名称: 2-[13-[2-(4-Methoxyphenyl)ethynyl]pentacen-6-yl]ethynyl-tri(propan-2-yl)silane
• 英文别名: 2-[13-[2-(4-methoxyphenyl)ethynyl]pentacen-6-yl]ethynyl-tri(propan-2-yl)silane
• CAS: 1051394-93-4
• 化学式: C₄₂H₄₀OSi
• 分子量: 588.865
• InChiKey: NYSITCHLBZKNDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[13-[2-(4-Methoxyphenyl)ethynyl]pentacen-6-yl]ethynyl-tri(propan-2-yl)silane 、 四氰基乙烯 以 二氯甲烷 为溶剂， 反应 24.0h， 以74%的产率得到3-[2-(4-Methoxyphenyl)ethynyl]-14-[2-tri(propan-2-yl)silylethynyl]hexacyclo[14.6.2.02,15.04,13.06,11.017,22]tetracosa-2,4,6,8,10,12,14,17,19,21-decaene-23,23,24,24-tetracarbonitrile
  参考文献：
  名称：

  Synthesis, physical properties, and chemistry of donor–acceptor-substituted pentacenes

  摘要：

  合成了带有电子给体和（或）电子受体基团的五环芴，即甲氧基，二烷基氨基和硝基芳基基团，以获得极化的五环芴。探讨了这些衍生物的光学、电化学和化学性质。研究了所选衍生物与四氰基乙烯（TCNE）的环加成反应，并基于密度泛函理论（DFT）计算对实验结果进行了解释。X射线晶体学数据提供了固态分子结构和分子间相互作用的见解。

  DOI：

  10.1139/cjc-2016-0450
• 作为产物：
  描述：

  6-((4-methoxyphenyl)ethynyl)-13-((triisopropylsilyl)ethynyl)-6,13-dihydropentacene-6,13-diol 在 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以87%的产率得到2-[13-[2-(4-Methoxyphenyl)ethynyl]pentacen-6-yl]ethynyl-tri(propan-2-yl)silane
  参考文献：
  名称：

  Exploring Electronically Polarized Pentacenes

  摘要：

  Unsymmetrically functionalized pentacenes with electron-rich and/or -poor substituents at the 6- and 13-positions were synthesized. The electronic influence was evaluated by solution-state UV-vis absorption and emission spectroscopies. These materials exhibit good solubility in common organic solvents and are stable in the presence of air and water.

  DOI：

  10.1021/ol801464k

文献信息

• Exploring Electronically Polarized Pentacenes
  作者：Dan Lehnherr、Robert McDonald、Rik R. Tykwinski

  DOI：10.1021/ol801464k

  日期：2008.10.2

  Unsymmetrically functionalized pentacenes with electron-rich and/or -poor substituents at the 6- and 13-positions were synthesized. The electronic influence was evaluated by solution-state UV-vis absorption and emission spectroscopies. These materials exhibit good solubility in common organic solvents and are stable in the presence of air and water.
• Synthesis, physical properties, and chemistry of donor–acceptor-substituted pentacenes
  作者：Dan Lehnherr、Matthias Adam、Adrian H. Murray、Robert McDonald、Frank Hampel、Rik R. Tykwinski

  DOI：10.1139/cjc-2016-0450

  日期：2017.3

  Pentacenes bearing electron-donating and (or) -withdrawing groups, namely methoxy-, dialkylamino-, and nitroaryl moieties, are synthesized to afford polarized pentacenes. The optical, electrochemical, and chemical properties of these derivatives are explored. The cycloaddition reaction of selected derivatives with tetracyanoethylene (TCNE) is explored, and the experimental results are rationalized on the basis calculations using density functional theory (DFT). X-ray crystallographic data provides insight into the molecular structure and intermolecular interactions present in the solid state.

  合成了带有电子给体和（或）电子受体基团的五环芴，即甲氧基，二烷基氨基和硝基芳基基团，以获得极化的五环芴。探讨了这些衍生物的光学、电化学和化学性质。研究了所选衍生物与四氰基乙烯（TCNE）的环加成反应，并基于密度泛函理论（DFT）计算对实验结果进行了解释。X射线晶体学数据提供了固态分子结构和分子间相互作用的见解。